The Future Self
Conversation Starters by JamSocial
Updated February 17, 2026
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What’s one thing you want to be able to do by this time next year?
If you could see a 'spoiler' for one area of your life, would you want to know?
If you could write a letter to yourself 10 years from now, what would the first sentence be?
What is a skill you want to master before you turn 50?
What’s one place you are determined to visit in the next five years?
What is a 'small win' you want to achieve by the end of this month?
If you were to write an autobiography, what would the title of the next chapter be?
What’s a hobby you’ve always wanted to pick up but have been putting off?
What does 'success' look like to you in a single sentence?
If you could change one thing about your daily routine starting tomorrow, what would it be?
What’s a 'risk' you’re currently contemplating that scares you a little?
What is a habit you have now that you hope your 80-year-old self still has?
How do you want your 'inner circle' of friends to look in five years?
What is something you’re doing today that your future self will thank you for?
If you could tell your future self one thing to never forget, what would it be?
What is a version of 'success' you've had to unlearn to keep your peace?
In what area of your life are you most hoping for a 'breakthrough' right now?
How do you want your relationship with your family to evolve as you get older?
What is a talent you’re currently 'sitting on' that you want to share with the world?
What’s a piece of wisdom you hope to be known for one day?
If you met your 10-years-older self today, what is the first question you’d ask them?
What are you doing today to ensure you don't have 'the same year' 40 times in a row?
What is the biggest 'gift' you are currently working to give your future self?
What do you want your legacy to be in the lives of the people who haven't even met you yet?
If you knew you were guaranteed to succeed, what is the one thing you’d start tomorrow?
What is a part of your identity that you are currently outgrowing?
When you look back on your life from your deathbed, what do you think you’ll regret *not* doing?
How are you currently preparing yourself for the person you want to become?
What does 'wholeness' look like for you in the next decade?
If you could be remembered for only one thing, what would it be?